1999–2000 Port Vale F.C. season

The pre-season saw Brian Horton sign Jeff Minton (Brighton & Hove Albion), Tommy Widdrington (Grimsby Town), and Steve Rimmer (Manchester City) on free transfers.

[2] The Vale ended the year in solid form, unbeaten in seven games, despite just two victories (over rivals Crewe Alexandra and against Sheffield United at Bramall Lane).

In March, Horton made two key signings, bringing two young players that would be with the club for several years to come: Irish midfielder Micky Cummins (Middlesbrough) and goalkeeper Mark Goodlad (Nottingham Forest).

[2] At the end of the season numerous players were allowed to leave on free transfers: eight-year club veteran goalkeeper Paul Musselwhite (Hull City); five-year club favourite Ian Bogie (Kidderminster Harriers); Wayne Corden (Mansfield Town); Stewart Talbot (Rotherham United);[3] Mark Snijders (AFC '34); Kevin Pilkington (Aberystwyth Town); and Steve Rimmer (Marine).

Meanwhile, the club's board increased to five members: Bill Bell (chairman), Andrew Bellfield, Paul Wright, Neil Hughes, and Charles Machin.

In the FA Cup, Vale lost 2–0 to Premier League club Leeds United at Elland Road to exit the competition in the Third Round.

In the 2–1 defeat at the Deva Stadium, both sides finished the game with ten men, and as the return leg was a 4–4 draw, Chester achieved a 6–5 aggregate win.